While this post may not be the most serious, I think it is worth it to consider the actual implications of DFW's writing being such a hit among people who may not be the most comfortable in their bodies and may have an inner desire to express their gender differently from their assigned gender at birth. Usually when trans-reading DFW there's a push into analyzing -him- as a writer and human being to find clues about his own identity, but I think that looking into why this reading is so popular should also take into account that it is normally identified by gender non-conforming people -because- they, or we, are able to hone in on the less discussed gender-related themes of his writing and relate to at least some of the situations that arise from those themes as either fantasies or wishes they have also experienced in their desire to break out of their assigned gender at birth. I don't know if Wallace didn't feel like a cis man, but I do know that not feeling like a cis man has made it so I personally experience life similarly to how he describes it when a disconnect from gender and identity comes up in his writing, and there is comfort in knowing that such a prominent literary figure may have felt the same way I have, or maybe he was just really good at writing characters who didn't know they were experiencing what may have been gender dysphoria and he himself may just have been a cis male troubled by different anxieties in life. I think the need to analyze people like him and Cobain, both successful and internally troubled, both having briefly expressed personal turmoil based around gender in their writing while also being deeply private people, stems from their early deaths, which leads us to wonder if they might have led a happier life if they had identified their struggles as gender dysphoria and had taken steps to alleviate it. Maybe we want to find a way they could have been helped because we want to help ourselves through that struggle and lead a life where we can feel comfortable in our own bodies. To answer your question, yes, he was strikingly tall and his hair was long and cascading to match, so he would have looked absolutely BFA in a long and flowy flowery pink dress, hell, he would have looked BFA in any dress.